Br[CH2:2][C:3]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)=O.[CH:18]([NH2:20])=[S:19]>C1COCC1.C(OCC)(=O)C>[S:19]1[CH:2]=[C:3]([CH:5]2[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)[N:20]=[CH:18]1The title compound from Step B above (500 mg, 1.63 mmol) was combined with thioformamide (100 mg, 1.63 mmol) in 5 mL of THF, warmed to 60° C., and stirred overnight. The mixture was cooled to RT and diluted with ethyl acetate. The solution was then washed with water followed by brine. The organics were dried over magnesium sulfate, filtered and concentrated under vacuum. Purification via preparative TLC plates (3×1000 μM) eluting with 60% ethyl acetate/hexane afforded the title compound (282 mg, 63%) as a clear oil. ESI-MS calculated for C13H20N2O2S: Exact Mass: 268.12. Found: 169.12 (M-Boc)+ and 291.14 (MNa)+.
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